NecroX-5 mesylate | CAS#1383718-29-3 | necrosis/necroptosis inhibitor

NecroX-5 mesylate
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 561380

CAS#: 1383718-29-3 (mesylate)

Description: NecroX-5 is an inhibitor of necrosis/necroptosis. NecroX-5 has been shown to scavenge mitochondrial reactive oxygen and nitrogen species, and thus preventing necrotic cell death against various kinds of oxidative stress in several tissues, including the brain.

Chemical Structure

NecroX-5 mesylate

CAS# 1383718-29-3 (mesylate)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 561380
Name: NecroX-5 mesylate
CAS#: 1383718-29-3 (mesylate)
Chemical Formula: C27H39N3O9S3
Exact Mass: 0.00
Molecular Weight: 645.801
Elemental Analysis: C, 50.22; H, 6.09; N, 6.51; O, 22.30; S, 14.89

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 450
10mg	USD 720
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Related CAS #: 1120332-90-2 (free base) 1526790-45-3 (HCl) 1383718-29-3 (mesylate) 1526790-48-6 (HBr) 1526790-50-0 (sulfate),

Synonym: NecroX-5; NecroX 5; NecroX5;

IUPAC/Chemical Name: 5-[(1,1-Dioxido-4-thiomorpholinyl)methyl]-2-phenyl-N-[(tetrahydro-2H-pyran-4-yl)methyl]-1H-indol-7-amine dimesylate

InChi Key: ZWWWDIWEZYRVMB-UHFFFAOYSA-N

InChi Code: InChI=1S/C25H31N3O3S.2CH4O3S/c29-32(30)12-8-28(9-13-32)18-20-14-22-16-23(21-4-2-1-3-5-21)27-25(22)24(15-20)26-17-19-6-10-31-11-7-19;2*1-5(2,3)4/h1-5,14-16,19,26-27H,6-13,17-18H2;2*1H3,(H,2,3,4)

SMILES Code: O=S1(CCN(CC2=CC3=C(NC(C4=CC=CC=C4)=C3)C(NCC5CCOCC5)=C2)CC1)=O.OS(=O)(C)=O.OS(=O)(C)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:

Product Data

Instruction:

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Biological target:	NecroX-5 is an inhibitor of necrosis/necroptosis.
In vitro activity:	NX-5 (10 μM and 20 μM) treatment significantly reduced melanoma cell migration (p < 0.01). Additionally, NX-5 (20 μM) treatment significantly decreased the mRNA and protein expression levels of Cdc42, Rac1, and RhoA in melanoma cells compared with the untreated group (p < 0.001 and p < 0.05, respectively). Reference: J Clin Med. 2021 Jun 25;10(13):2790. https://pubmed.ncbi.nlm.nih.gov/34201921/
In vivo activity:	This study utilized HR (hypoxia/reoxygenation)-treated rat hearts and lipopolysaccharide (LPS)-treated H9C2 culture cells in the presence or absence of NecroX-5 (10 µmol/L) treatment as experimental models. Addition of NecroX-5 signifi cantly increased decorin (Dcn) expression levels in HR-treated hearts. In contrast, expression of transforming growth factor beta 1 (TGFβ1) and Smad2 phosphorylation (pSmad2) was strongly attenuated in NecroX-5-treated hearts. Reference: Korean J Physiol Pharmacol. 2016 May;20(3):305-14. https://pubmed.ncbi.nlm.nih.gov/27162485/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	170.0	263.24

Preparing Stock Solutions

The following data is based on the product molecular weight 645.80 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:	1. Min L, Shu-Li Z, Feng Y, Han H, Shao-Jun L, Sheng-Xiong T, Jia-Yu T, Xiang-Zhi F, Dan F. NecroX-5 ameliorates bleomycin-induced pulmonary fibrosis via inhibiting NLRP3-mediated epithelial-mesenchymal transition. Respir Res. 2022 May 20;23(1):128. doi: 10.1186/s12931-022-02044-3. PMID: 35596212; PMCID: PMC9121617. 2. Moon GT, Lee JH, Jeong SH, Jin SW, Park YM. NecroX-5 Can Suppress Melanoma Metastasis by Reducing the Expression of Rho-Family GTPases. J Clin Med. 2021 Jun 25;10(13):2790. doi: 10.3390/jcm10132790. PMID: 34201921; PMCID: PMC8267632. 3. Fang XZ, Ge YL, Chen ZY, Shu HQ, Yang YY, Yu Y, Zhou XJ, Chen L, Cui SN, Wang YX, Yao SL, Shang Y. NecroX-5 alleviate lipopolysaccharide-induced acute respiratory distress syndrome by inhibiting TXNIP/NLRP3 and NF-κB. Int Immunopharmacol. 2020 Apr;81:106257. doi: 10.1016/j.intimp.2020.106257. Epub 2020 Feb 7. PMID: 32044659. 4. Thu VT, Kim HK, Long le T, Thuy TT, Huy NQ, Kim SH, Kim N, Ko KS, Rhee BD, Han J. NecroX-5 exerts anti-inflammatory and anti-fibrotic effects via modulation of the TNFα/Dcn/TGFβ1/Smad2 pathway in hypoxia/reoxygenation-treated rat hearts. Korean J Physiol Pharmacol. 2016 May;20(3):305-14. doi: 10.4196/kjpp.2016.20.3.305. Epub 2016 Apr 26. PMID: 27162485; PMCID: PMC4860373.
In vitro protocol:	1. Min L, Shu-Li Z, Feng Y, Han H, Shao-Jun L, Sheng-Xiong T, Jia-Yu T, Xiang-Zhi F, Dan F. NecroX-5 ameliorates bleomycin-induced pulmonary fibrosis via inhibiting NLRP3-mediated epithelial-mesenchymal transition. Respir Res. 2022 May 20;23(1):128. doi: 10.1186/s12931-022-02044-3. PMID: 35596212; PMCID: PMC9121617. 2. Moon GT, Lee JH, Jeong SH, Jin SW, Park YM. NecroX-5 Can Suppress Melanoma Metastasis by Reducing the Expression of Rho-Family GTPases. J Clin Med. 2021 Jun 25;10(13):2790. doi: 10.3390/jcm10132790. PMID: 34201921; PMCID: PMC8267632.
In vivo protocol:	1. Fang XZ, Ge YL, Chen ZY, Shu HQ, Yang YY, Yu Y, Zhou XJ, Chen L, Cui SN, Wang YX, Yao SL, Shang Y. NecroX-5 alleviate lipopolysaccharide-induced acute respiratory distress syndrome by inhibiting TXNIP/NLRP3 and NF-κB. Int Immunopharmacol. 2020 Apr;81:106257. doi: 10.1016/j.intimp.2020.106257. Epub 2020 Feb 7. PMID: 32044659. 2. Thu VT, Kim HK, Long le T, Thuy TT, Huy NQ, Kim SH, Kim N, Ko KS, Rhee BD, Han J. NecroX-5 exerts anti-inflammatory and anti-fibrotic effects via modulation of the TNFα/Dcn/TGFβ1/Smad2 pathway in hypoxia/reoxygenation-treated rat hearts. Korean J Physiol Pharmacol. 2016 May;20(3):305-14. doi: 10.4196/kjpp.2016.20.3.305. Epub 2016 Apr 26. PMID: 27162485; PMCID: PMC4860373.

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1: Park JH, Kim HK, Jung H, Kim KH, Kang MS, Hong JH, Yu BC, Park S, Seo SK, Choi IW, Kim SH, Kim N, Han J, Park SG. NecroX-5 prevents breast cancer metastasis by AKT inhibition via reducing intracellular calcium levels. Int J Oncol. 2017 Jan;50(1):185-192. doi: 10.3892/ijo.2016.3789. Epub 2016 Dec 5. PubMed PMID: 27922686.

2: Kim HI, Paik SS, Kim GH, Kim M, Kim SH, Kim IB. Neuroprotective effect of NecroX-5 against retinal degeneration in rodents. Neuroreport. 2016 Oct 19;27(15):1128-33. doi: 10.1097/WNR.0000000000000666. PubMed PMID: 27541272.

3: Thu VT, Kim HK, Long le T, Thuy TT, Huy NQ, Kim SH, Kim N, Ko KS, Rhee BD, Han J. NecroX-5 exerts anti-inflammatory and anti-fibrotic effects via modulation of the TNFα/Dcn/TGFβ1/Smad2 pathway in hypoxia/reoxygenation-treated rat hearts. Korean J Physiol Pharmacol. 2016 May;20(3):305-14. doi: 10.4196/kjpp.2016.20.3.305. Epub 2016 Apr 26. PubMed PMID: 27162485; PubMed Central PMCID: PMC4860373.

4: Degterev A, Linkermann A. Generation of small molecules to interfere with regulated necrosis. Cell Mol Life Sci. 2016 Jun;73(11-12):2251-67. doi: 10.1007/s00018-016-2198-x. Epub 2016 Apr 5. Review. PubMed PMID: 27048812.

5: Thu VT, Kim HK, Long le T, Nyamaa B, Song IS, Thuy TT, Huy NQ, Marquez J, Kim SH, Kim N, Ko KS, Rhee BD, Han J. NecroX-5 protects mitochondrial oxidative phosphorylation capacity and preserves PGC1α expression levels during hypoxia/reoxygenation injury. Korean J Physiol Pharmacol. 2016 Mar;20(2):201-11. doi: 10.4196/kjpp.2016.20.2.201. Epub 2016 Feb 23. PubMed PMID: 26937217; PubMed Central PMCID: PMC4770111.

6: Kang DH, Kim YH, Kim MK, Kim MS, Chung KJ. Effects of NecroX-5 on the Survival of a Random Pattern Skin Flap in Mice. Arch Plast Surg. 2015 Nov;42(6):789-91. doi: 10.5999/aps.2015.42.6.789. Epub 2015 Nov 16. PubMed PMID: 26618130; PubMed Central PMCID: PMC4659996.

7: Li X, Kwon O, Kim DY, Taketomi Y, Murakami M, Chang HW. NecroX-5 suppresses IgE/Ag-stimulated anaphylaxis and mast cell activation by regulating the SHP-1-Syk signaling module. Allergy. 2016 Feb;71(2):198-209. doi: 10.1111/all.12786. Epub 2015 Nov 23. PubMed PMID: 26456627.

8: Kim SR, Kim DI, Kim SH, Lee H, Lee KS, Cho SH, Lee YC. NLRP3 inflammasome activation by mitochondrial ROS in bronchial epithelial cells is required for allergic inflammation. Cell Death Dis. 2014 Oct 30;5:e1498. doi: 10.1038/cddis.2014.460. PubMed PMID: 25356867; PubMed Central PMCID: PMC4237270.

9: Wang B, Xiao JL, Ling YH, Meng XJ, Wu B, Yang XY, Zou F. BNIP3 upregulation by ERK and JNK mediates cadmium-induced necrosis in neuronal cells. Toxicol Sci. 2014 Aug 1;140(2):393-402. doi: 10.1093/toxsci/kfu091. Epub 2014 May 13. PubMed PMID: 24824807.

10: Lee SR, Lee SJ, Kim SH, Ko KS, Rhee BD, Xu Z, Kim N, Han J. NecroX-5 suppresses sodium nitroprusside-induced cardiac cell death through inhibition of JNK and caspase-3 activation. Cell Biol Int. 2014 Jun;38(6):702-7. doi: 10.1002/cbin.10242. Epub 2014 Feb 5. PubMed PMID: 24446382.

11: Song JJ, Chang J, Choi J, Im GJ, Chae SW, Lee SH, Kwon SY, Jung HH, Chung AY, Park HC, Choi J. Protective role of NecroX-5 against neomycin-induced hair cell damage in zebrafish. Arch Toxicol. 2014 Feb;88(2):435-41. doi: 10.1007/s00204-013-1124-3. Epub 2013 Sep 13. PubMed PMID: 24030356.

12: Park MK, Lee BD, Chae SW, Chi J, Kwon SK, Song JJ. Protective effect of NecroX, a novel necroptosis inhibitor, on gentamicin-induced ototoxicity. Int J Pediatr Otorhinolaryngol. 2012 Sep;76(9):1265-9. doi: 10.1016/j.ijporl.2012.05.016. Epub 2012 Jun 15. PubMed PMID: 22704672.

13: Thu VT, Kim HK, Long le T, Lee SR, Hanh TM, Ko TH, Heo HJ, Kim N, Kim SH, Ko KS, Rhee BD, Han J. NecroX-5 prevents hypoxia/reoxygenation injury by inhibiting the mitochondrial calcium uniporter. Cardiovasc Res. 2012 May 1;94(2):342-50. doi: 10.1093/cvr/cvs122. Epub 2012 Mar 16. Erratum in: Cardiovasc Res. 2012 Jul 1;95(1):134. PubMed PMID: 22425903.

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